Ask the Awkward Question: You Might Get an Awesome Answer

Written by on 18 Mar 2014

Let’s take a quick stroll down memory lane, shall we?

I just don’t think we do this enough.

So, let’s dive in!

First, think about your best friend…

Who is she? How long have you known her? Do you remember how you met?

Make a note of that.

Next, think about your first job…

What was it? How long ago did you get it? Do you remember how you found out about it?

Make a note of that, too.

Finally, think about your last roommate…

Who was he? How do you know him? Do you remember how you decided to live together?

Make a note of that, as well.

Now, time to synthesize.

For some of you, this exercise may bring up good memories or bad memories… or both. It may remind you of circumstances that were carefully crafted or others that were entirely out of your control… or both. It may even make you realize that the presence of some of the most important things in your life—your best friend, your first job, or your last roommate, for instance—happened because of something completely and utterly random.

Or maybe, just maybe, you might see a pattern start to emerge.

For me, there is a definite and distinct pattern related to all three of these things.

And here it is…

I, Tracy Timm, am…




And you thought you were about to get a mini-dose of Buddha-like knowledge.

Sorry ‘boutcha.

No wise words or nerdy nuggets here—just the simple truth. I have spent most of my life trying to play it cool (whatever it is) and hold it all together (again, it remains uber-nebulous), but when I’m truly honest with myself, I’ve come to realize this unavoidable fact.

Some of the best things that have come into my life appeared simply because I am and always will be…




Turns out, I am also…




And because I’m both awkward and curious, I tend to ask uncomfortable, random, and unexpected questions.

Of total strangers.

On the reg.

It was fortuitous questions such as these, and not necessarily my awkwardness or curiosity themselves, that led me to my best friend, my first job, and my last roommate.

And since we’re already on memory lane, I’ll go ahead and share these three stories with you.

Hopefully, as you read them, your pattern—awkward, curious, or otherwise—will begin to emerge.

My Best Friend:

When I was 16, I had to go through what almost every Catholic youth dreads—Confirmation.

For those of you who are not Catholic, just imagine a 6-month process of classes, retreats, group meetings, homework, and tests that are designed to fully indoctrinate you into the faith and enable you to become a contributing member of the Church.

Now, again, imagine yourself as a 16-year-old, and please, oh please, try and convince me that you would be excited about something like this.

Ya… you can’t.

We dread Confirmation for all kinds of reasons, but mostly because, hey, we are 16 and don’t want to do homework for church, and just want to be with our friends, and blah, blah, blah insert other juvenile excuse here.

But the best and most juvenile excuse of them all is the fact that, well…

We just don’t know anybody!

And certainly don’t want to meet anyone new.

Especially at church.

Which is really sad.

Because if I had given in to that juvenile temptation, I never would have met Lucy.

So, here’s what happened.

Of course, to add insult to injury, Confirmation began by throwing all of these teens who didn't know each other into a weekend-long retreat with no contact to the outside world.


And of course, that process begins by choosing a cabin to sleep in for the entire weekend.

Even more awesome.

I’m sorry, but this is just some 7th circle of Hell type torture for high school kids.

Because, how in the world, are you supposed to decide where to sleep when you don’t know anybody?!

But nonetheless, I knew I wasn’t going to sleep on the ground, so I reluctantly walked up to the sign in sheets.

At the exact same time that she did.

We stood there next to each other for about a whole minute just looking down at the layouts of different rooms and beds… contemplating our options… contemplating running away from our options…

And then, I got awkward.

And curious.

I just looked up at her and said what no one wants to admit:

Ugh, I don’t know ANYBODY.

Do you?

And you know what her answer was?


Wanna stay together?


It’s been 10 years since that fateful day at the sign-in sheet, and Lucy remains one of my best and closest friends in the entire world. Despite going to different colleges and living in different cities, we’ve been able to keep in touch, visit on occasion, and most importantly, support each other through some of the best and worst times in our lives. I adore her.

All because I asked the scary, awkward, curious question.

My First Job

The summer before I left for college, I was 18 and totally broke.

I think that’s probably true of most people before and during college … but you get the idea.

With minimal corporate experience, but two eye-opening years at El Chico Mexican Café under my belt, I started looking around for a job as a server.

Having seen the depressingly-high ratio of frustration to compensation at The Chico, I decided to aim for something a bit, umm, more efficient.

That’s a PC way to say nicer restaurant, right?

Anyway, I began what would become the wildest of goose chases as I desperately searched for a higher-end restaurant that was willing to train me for only three months of service before I left for school. Apparently, a week-long investment in teaching sauces and wine pairings is worth more than three months.

Thus, I struggled.

On what was about to be my last ditch effort, I walked into Sonoma Grill, a cute but fancy Italian restaurant in Flower Mound, Texas.

Now, if you’ve never worked at a restaurant (which everyone should at some point, especially if you ever plan on eating out), here’s a little industry secret about finding the ‘decision-makers’ and getting them to ‘say yes.’

Only show up between 2 and 4pm.

If you go at any other time, whoever you meet will be too busy or too distracted to give you the time of day. Coincidently, they will immediately dislike you for ‘getting them weeded’ in the middle of ‘the rush.’ You’ll never hear back from them.

Just don’t do it.

Anyway, I showed up at 3pm, and started scanning the room for a manager working on a schedule.

Side note—this was before apps like HotSchedules and ShiftPlanning existed. Back in the day, people actually wrote out schedules by hand, generally during the down time between lunch and dinner.

Scandalizing, I know.

But there he was, sitting in the bar, just where I expected him to be.

So, confidently, I walked up, tapped this man on the shoulder, and handed him my resume.

That’s how I met Aaron.

Who, by the way, was not a manager at Sonoma Grill.


He turned to me and said:

Sorry, I don’t work here. I’m a recruiter. But, good luck!


As I walked back the front to wait at the host stand, my awkward curiosity got the better of me.

I had been recruited to play softball in college, so I turned around and asked the first question that came to mind:

What kind of recruiter?

An hour later, Aaron and I were discussing his business as a corporate recruiter in the logistics industry. It was his job to source, screen, and staff professionals ranging in function from warehouse manager to CEO. He had been running the company on his own for several years, and guess what?

He needed some help.

Yahtzee, again!

Aaron and I worked together that entire summer as I prepared to leave for school. He taught me the power of truthful and honest business, allowed me to cut my teeth on scary projects before I knew I should be scared, and guided me as a friend and mentor through a big transition in my life. He and I remain friends to this day, and I’ll never be able to thank him enough for his impact and influence.

All because I asked the scary, awkward, curious question.

My Last Roommate

Spring semester of my senior year in college, I had resigned myself to homelessness.

I had landed the ever-elusive job (spring of 2010, they were hard to come by), but I was still chasing the even more-elusive, perfect roommate.

My job was taking me almost 2000 miles away from home, so I knew that living alone was just not an option. I was prepared to feel a little lost and disconnected, but the thought of doing that without a roommate was unbearable.

That being said, I didn’t know a single person who wanted to live in Stamford, Connecticut.

Thus, homelessness.

After my initial inventory of friends and a brief but terrifying foray into the world of Craigslist roommates, I was gingerly warming myself up to the idea of living… gasp… alone.

Then, Myrtle happened.

I went to college in a place that is really, really, really cold. So, we have an annual tradition of ending the year with a much-needed road trip to a wildly-inconvenient beach—Myrtle.

Myrtle Beach is the stuff of legends. It’s where new relationships begin. It’s where friendships are solidified. It’s where nights are spent dancing in cages at Sp-oads (Spanish Toads) until 4 in the morning.

And apparently, it’s also where roommates are found.

So there I was, standing on the beach, partaking in an adult beverage, and waiting for my turn to ride on the inflatable lobster (named Larry, of course), when Dallas showed up.

Dallas was a friend of a friend, slightly above acquaintance and slightly below pal. I think the best way to describe our relationship is that we knew of each other, rather than actually knowing each other. All good things, of course.

But like I said, Myrtle brings people together.

We started talking about graduation, life after Yale, and plans for the future. I guess the urgency of finding a roommate before going back to Texas for the summer was really starting to get to me, because I just got awkward and curious and said:

Everyone is moving to Manhattan. No one wants to live in Stamford with me. What are you going to do?

If you’re sensing a pattern here, you can probably guess his response:

I’m moving to Stamford.



No way, we should TOTALLY live together.

I should have thanked that adult beverage personally for helping me channel my inner Valley Girl.

We spent the next couple hours, in between impromptu sprints to the ocean and back, talking about where to live (downtown) and how to decorate (urban-Texas theme). I was fully prepared for him to show up the next morning with no recollection of our conversation and no desire to live together.

Instead, we decided on a place the following day and put down our deposit a week later.

Without Dallas, my first year out of college would have been dreadful. He taught me how to laugh amidst uncertainty, how to work insanely hard, and how to properly drink Guinness. While he is back in Connecticut and I am now in Texas, we keep in touch and continue to support each other no matter the distance.

All because I asked the scary, awkward, curious question.

Take a look at your life and see where your patterns are. Then take that awkwardness, curiosity, or other awesome trait, and continue to use it!

Ask the awkward question-- you never know the answer you might get.


What patterns do you see in your own life? Which important people or experiences have been brought to you out of these interactions?

I believe that every greatness we enjoy right now can be traced back to one person, conversation, or observation that provided a turning point in our lives. I’d love to hear if you believe this, too.

Did this story resonate with you? Or did it make you think of a story of your own? Share your story or your reaction in the comments below.

Because sharing stories an instinctual, powerful way to touch the hearts of others and change the world around us.

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  1. Ben Smith   On   19 Mar 2014 at 1:18 pm

    I started a story inspired by this, but started rambling and don’t have time to finish it up today. But you’re Catholic? Heck, come with Kristen and join Jen and me at St Anne’s for this mission talk thingie tonight. It’s pretty good!

  2. Ben Smith   On   24 Mar 2014 at 10:31 pm

    Ahhhh the job/roommate stories bring me back to my fresh out of college life. Just like it’s good to be your awkward, curious self, I’ve found a lot of good from being my… I guess opportunistic, fly-by-the-seat-of-my-pants-ish self.

    Via pursuit of a job in Austin, Texas the company I was interviewing with wanted to send me to their office in Monterrey, California. I didn’t quite know where that was, but it sounded awesome… and expensive, so I bumped up my asking salary and got the job! So at 6 am two weeks later, with a loaded U-haul hitched to my truck, I hugged my mom goodbye and was headed west! As the sun came up, the wave of tears I’d caught from Mom upon parting dissolved into excitement, freedom, rowed-down windows, and some loud ZZ Top.

    I had no idea where I’d live when I got to Monterrey. I knew no one! My company allowed me up to one week at a hotel while apartment hunting. I showed up on a Saturday, met my new boss, and was given a general tour. Sunday, I apartment hunted.

    One ad sounded relatively reasonable for a 1/1 house! I called and the first question the person asked… “How tall are you?”

    “Six foot five,” I answered. Laugher was all I heard on the other end… until the guy told me the ceilings in this house were six feet. Dang it.

    So… the search continued. Prices were high out there and I had always loved having roommates, anyway. I apartment hunted fully accepting the fact that I would be breaking down in tears of loneliness living alone 2000 miles from home in a town where I knew no one, but that was life. Cowboy up.

    Monday morning, I was on the job.

    This was a large scale tree transplanting company that would excavate, move, and replant massive trees with cranes, semi-trucks, and a variety of other wildly engineered machinery. Our main clients were casinos, golf courses, and high end developments that want a big tree “here” yesterday, not 30 years from now, and have the money to throw at such endeavors.

    So… after my higher education at Texas A&M learning the finer points of Forest Science, first day on the job I found myself in a hole digging a ditch…

    I gotta say, the ocean view from Pebble Beach golf course on a sunny October day is about the best setting you could ever ask to be digging a ditch! So I wasn’t complaining! I was getting to know my crew, and working on some serious Spanglish lessons with them as I began to learn what all is involved in the laborious and multi-faceted niche business of large tree transplanting.

    When us ditch diggers had done all the rootball shaping we could around a tree, we’d jump out of the hole and an excavator would dig out the excess dirt and deepen the ditch. We’d jump back in and do the finer digging, shaping, and root pruning with our shovels, loppers, axes, and pickaxes. Then, it was out of the hole to let the excavator dig some more. We’d repeat this process until we had a tree with a nice bowl-shaped rootball ready for wrapping.

    The guy operating the excavator was named Mike Bleck.

    Mike Bleck… with his sailor-like know-how, confidence, and vocabulary… was keeping me heartily entertained through our work day… we bantered back I forth in that way guys do that might leave you shocked and insulted if you’re not tough and/or hip to sarcasm, but will make you grin and dish out something even more ridiculous if you are. This is a very important art form for the new guy on a construction site.

    Mike: “So Ben from Texas, I hear you play some country music?”
    Me: “Yep”
    Mike: “You any good?”
    Me: “Well heck yes.”
    Mike: “As good as Garth Brooks?”
    Me: “Garth Brooks?? [said with exaggerated shock, surprise, and disgust] Where the Hell am I?”
    Mike: “Hahaha!! Well what are you doing in that hole then?”
    Me: “How am I supposed to write the working man’s music without spending a little time in a hole?”

    Mike was 27 and I, 22. I’d later learn he was the top operator for our neighboring development company who happened to be helping us dig trees that day. He also ran his own rock hauling company simultaneously, continuously relaying info to his truck driver via cell phone throughout the day from the cab of the excavator. One guy, making two incomes at the same time. This was no ordinary 27 year-old.

    When the shim plate fell out and rendered the excavator useless (a part who’s existence I was unaware of until this moment) Mike grabbed some wrenches from his truck, jumped up, and fixed it. This guy could build, fix, operate, do ANYTHING. And well! Watching a track loader fill in a hole, while operated by Mike, was not too different from watching a damn ballet! He could make machines dance.

    Mike: I hear you haven’t found a place to stay yet.
    Me: “Nah, still hunting. Just got here two days ago.
    Mike: Well, I’ve got one roommate already, but we’ve got a spare room.

    So Mike owned his own house… small, but nice and clean. I’d come from College Station, TX… arguably the most conservative and redneck hotbed in Texas. The homes of Monterrey, California all seemed to have little Hondas and Subarus with rather yuppie-ish bumper stickers on them parked out front… except for Mike’s. Between Mike and his electrician roommate Matt, they must have had five quad-cab, one ton trucks parked out front! That helped sell me on it, but the the fork lift parked in the back yard is what REALLY drove it home. I was home. It was also less than three miles from work and the price was right! I played Matt and Mike a song I’d written about… you guessed it… trucks, and they were sold on me!
    (Note: this was in 2004, well before the age of rabbles upon rabbles of relentlessly cheesy and formulaic songs about trucks. Mine’s awesome and predates all that crap.)

    So… day one on the job and I had a place to live, and some new buddies, Mike and Matt.

    Through the next months, Mike’s friendship made my transition to the West Coast more fun and exciting than I could have ever planned, and basically void of homesickness whatsoever. Nine years later, we are still good friends and get together for wild adventures once or twice a year.

    I don’t think I’ve ever been let down by being opportunistic, and flying by the seat of my pants! The end!

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